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2-Bromopyridine

2-Bromopyridine structure

CAS No:
109-04-6
Formula:
C5H4BrN
Chemical Name:
2-Bromopyridine
Synonyms:
Pyridine,2-bromo-;2-Bromopyridine;o-Bromopyridine;β-Bromopyridine;2-Pyridyl bromide;NSC 8031;2-Bromopyridin;Pyridin-2-yl bromide
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

dark red liquid

2-Bromopyridine is an organic compound with the formula BrC5H4N. It is a colorless liquid that is used as an intermediate in organic synthesis. It can be prepared from 2-aminopyridine via diazotization followed by bromination. It reacts with butyllithium to give 2-lithiopyridine, a versatile reagent.

2-bromopyridine is a monobromopyridine.

2-Bromopyridine Basic Attributes

Molecular Weight：

158

Exact Mass：

158.00

BRN：

105789

EC Number：

203-641-6

UNII：

7Z7MLC4VD8

NSC Number：

8031

DSSTox ID：

DTXSID6051564

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

1.4

Appearance：

Clear colorless to pale brown Liquid

Density：

1.6337 g/cm³ @ Temp: 20 °C

Melting Point：

<25 °C

Boiling Point：

194.8 °C

Flash Point：

130 °F

Refractive Index：

n 20/D 1.572(lit.)

Water Solubility：

Slightly miscible with water.

Storage Conditions：

Refrigerator

Vapor Pressure：

0.77 mmHg

Toxicity：

Abdominal cavity-mouse LDL0: 31.3 mg/kg

Flammability characteristics：

Thermal decomposition to emit toxic nitrogen oxides and bromide fumes

Safety Information

Packing level：

Hazard category：

6.1

Transport codes：

UN 2929 6.1/PG 2

wgk germany：

hazard class code：

10-24/25-36/37/38-23/24/25-20/21/22

safety instructions：

16-36/37-45-38-36/37/39-28A-26

RTECS Number：

US3850000

Marks：

T,Xn,F

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from food materials

Hazard note：

Toxic

Stability/Shelf Life：

Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides.

Precautionary statement(s)：

P280-P301 + P310 + P330-P302 + P352 + P310-P304 + P340 + P312-P305 + P351 + P338-P337 + P313

Hazard Statements：

H301-H310-H315-H319-H335

RIDADR：

UN 2929 6

GHS Classification：

|Danger|H226 (15.52%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 58 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

high toxic

2-Bromopyridine Use and Manufacturing

Methods of Manufacturing

Derived from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (above 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, then liquid bromine is added dropwise under salt bath freezing, the rate of addition is used to control the reaction temperature below -5°C Is appropriate. After the addition, dropwise add an aqueous solution of sodium nitrite, control the reaction temperature below 0°C, stir for 20-30 min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, collecting 88 ℃ -94 ℃/3333Pa distillate to obtain the finished product, the yield was 83.8%.

Uses

2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.Organic synthesis, pharmaceutical intermediates. In the pharmaceutical industry, it is used to synthesize diisopropyramine (propylpyramine phosphate) for heart diseases. It is used as a pharmaceutical intermediate. It is one of the important chemical raw materials for dimethyl sulfate. It is an important methylating agent. It is used in chemicals, medicine, pesticides, military industry, dyes, spices.

Manufacturing Info：

Pyridine, 2-bromo-: ACTIVE

Analysis Methods

Name	Column Shape	Active Phase(℃)	Retention index	Temperature Control	Method	Comments	Reference
Van Den Dool and Kratz RI, non-polar column, temperature ramp	Capillary	OV-1	988.0		temperature ramp	8. K/min; T_start: 35. C; T_end: 300. C	Gautzsch, R.Zinn, P.Use of incremental models to estimate the retention indexes of aromatic compoundsChromatographia1996, 43, 3/4, 163-176.

Computed Properties

Molecular Weight:158.00
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Exact Mass:156.95271
Monoisotopic Mass:156.95271
Topological Polar Surface Area:12.9
Heavy Atom Count:7
Complexity:56
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

Material

Pyridine

Benzene

Ethyl ketone

Downstream Products

2,2′-Bipyridine

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2-Bromopyridine CAS 109-04-6 C5H4BrN

CAS No.: 109-04-6

Content: 99%

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